120876-13-3Relevant academic research and scientific papers
Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetiola destructor, Drosophila mulleri and Contarinia pisi
Ferrarini, Renan S.,Comasseto, Joao V.,Dos Santos, Alcindo A.
experimental part, p. 2043 - 2047 (2010/03/04)
The components of the pheromone blend of Mayetiola destructor, Drosophila mulleri, and Contarinia pisi were synthesized in high enantiomeric excess (99% ee) from a common enantiopure dianion prepared from an enantiopure hydroxytelluride.
(Z,Z)-4,7-tridecadien-(S)-2-YL acetate: Sex pheromone of Douglas-fir cone gall midge, Contarinia oregonensis
Gries, Regine,Khaskin, Grigori,Gries, Gerhard,Bennett, Robb G.,King, G.G. Skip,Morewood, Petra,Slessor, Keith N.,Morewood, W. Dean
, p. 2283 - 2297 (2007/10/03)
Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50μg) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.
Synthesis of derivatives of (S)-2-alkanols, components of pheromones of Drosophila mulleri and Rhyzopertha dominica, from (S)-(+)-3,7-dimethylocta-1,6-diene
Ishmuratov,Kharisov,Botsman,Zorin,Tolstikov
, p. 1899 - 1901 (2007/10/03)
Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit fly Drosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borer Rhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyrcene.
Insect pheromones and their analogs. LX. Stereocontrolled synthesis of sex pheromones of Drosophila mulleri and Mayetiola destructor
Kharisov,Petukhova,Davletova,Ishmuratova,Zorin,Ishmuratov,Tolstikov
, p. 210 - 212 (2007/10/03)
Syntheses are developed for 2S-tridecyl-and 2S-tridec-10E-enylacetates, sex pheromones of the fruit fly Drosophila mulleri and the Hessian fly Mayetiola destructor, respectively, that are based on ethyl-3S-hydroxybutanoate, a product from enzymatic reduction of ethyl acetoacetate by the soil yeast strain "80-1.".
Studies on PPL catalyzed acetylation of 2-alkanols: Its application for the synthesis of 2-dodecanol and 2-tridecyl acetate, the pheromones of Crematogaster ants and Drosophila mulleri flies
Sharma, Anubha,Pawar, Archana S.,Chattopadhyay, Subrata
, p. 19 - 25 (2007/10/03)
Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.
Insect pheromone synthesis using Mn-salen catalyzed asymmetric epoxidation as a key step
Hamada,Daikai,Irie,Katsuki
, p. 2441 - 2451 (2007/10/03)
Enantioselective synthesis of three insect pheromones, (5Z, 13S)-5-tetradecen-13-olide, (9R)-decan-9-olide, and (S)-2-acetoxytridecane, has been achieved by using Mn-salen catalyzed asymmetric epoxidation as a key step.
Enantioselective Synthesis of (S)-(+)-2-Tridecanol Acetate, an Aggregation Pheromone Component of Drosophila mulleri
Enders, Dieter,Plant, Andrew
, p. 1241 - 1243 (2007/10/02)
The enantioselective synthesis of (S)-(+)-2-tridecanol acetate (ee = 93.5percent), an aggregation pheromone of Drosophila mulleri, is described.Key steps are the α-alkylation of the propiophenone SAMP-hydrazone (S)-2 (de 96percent) and the Baeyer-Villiger reaction of the ketone (S)-4.Key Words: (S)-(+)-2-Tridecanol acetate / SAMP-hydrazone / Baeyer-Villiger reaction / Pheromone, aggregation / Drosophila mulleri
Synthesis of (S)-(+)-parasorbic acid and (S)-(+)-2-tridecanol acetate: Bakers' yeast reductions of γ and δ ketosulfones
Gopalan, Aravamudan S.,Jacobs, Hollie K.
, p. 5575 - 5578 (2007/10/02)
The enantioselective reduction of 4-(p-toluenesulfonyl) butane-2-one and 5-(p-toluenesulfonyl) pentane-2-one with bakers' yeast gave the corresponding (S) alcohols in high optical purities and moderately good yields. The alcohol 2a was converted to (S)(+)parasorbic acid (4), while 2b was used for the preparation of (S)(+)-2-tridecanol acetate (7), using short synthetic sequences.
